Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from N-(pent-2-en-4-ynyl)-beta-lactams.
Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.
Peng
Yu
Y
Department of Chemistry, University of Nevada, Reno, Nevada 89557, USA.
Yu
Meng
M
Zhang
Liming
L